Crosslinking and decomposition reactions of epoxide functionalized polynorbornene. Part I. FTIR and thermogravimetric analysis

Chiniwalla, P.; Bai, Yiqun; Elce, Edmund; Shick, Robert A.; McDougall, W. Christopher; Allen, Sue Ann Bidstrup; Kohl, Paul A.

doi:10.1002/app.12234

Cited by 50 publications

(38 citation statements)

References 12 publications

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“…This reaction has been reported to be second order, first order in perstearic acid and in double bonds, with an activation energy of 51.2 kJ mol -1 (Hilker et al 2001). Oxygen in an epoxide ring can be attacked by acid causing the opening of the ring and the formation of a hydroxyl species and a carbocation (Chiniwalla et al 2003). Crosslinking can occur when the oxygen of an epoxide group is attacked by a carbocation (Chiniwalla et al 2003).…”

Section: Mechanism Of Epoxidation Reactionsmentioning

confidence: 99%

“…Oxygen in an epoxide ring can be attacked by acid causing the opening of the ring and the formation of a hydroxyl species and a carbocation (Chiniwalla et al 2003). Crosslinking can occur when the oxygen of an epoxide group is attacked by a carbocation (Chiniwalla et al 2003). A naturally epoxidised vegetable oil, vernonia oil, employed in formulations of alkyd and epoxy coating, consists of a triacylglycerol of vernolic (cis-12,13-epoxy-cis-9-octadecenoic) acid.…”

Section: Mechanism Of Epoxidation Reactionsmentioning

confidence: 99%

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Low temperature oxidation of linseed oil: a review

et al. 2012

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This review analyses and summarises the previous investigations on the oxidation of linseed oil and the self-heating of cotton and other materials impregnated with the oil. It discusses the composition and chemical structure of linseed oil, including its drying properties. The review describes several experimental methods used to test the propensity of the oil to induce spontaneous heating and ignition of lignocellulosic materials soaked with the oil. It covers the thermal ignition of the lignocellulosic substrates impregnated with the oil and it critically evaluates the analytical methods applied to investigate the oxidation reactions of linseed oil. Initiation of radical chains by singlet oxygen ( 1 Δ g ), and their propagation underpin the mechanism of oxidation of linseed oil, leading to the self-heating and formation of volatile organic species and higher molecular weight compounds. The review also discusses the role of metal complexes of cobalt, iron and manganese in catalysing the oxidative drying of linseed oil, summarising some kinetic parameters such as the rate constants of the peroxidation reactions. With respect to fire safety, the classical theory of self-ignition does not account for radical and catalytic reactions and appears to offer limited insights into the autoignition of lignocellulosic materials soaked with linseed oil. New theoretical and numerical treatments of oxidation of such materials need to be developed. The self-ignition induced by linseed oil is predicated on the presence of both a metal catalyst and a lignocellulosic substrate, and the absence of any prior thermal treatment of the oil, which destroys both peroxy radicals and singlet O 2 sensitisers. An overview of peroxyl chemistry included in the article will be useful to those working in areas of fire science, paint drying, indoor air quality, biofuels and lipid oxidation.

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Section: Mechanism Of Epoxidation Reactionsmentioning

confidence: 99%

Section: Mechanism Of Epoxidation Reactionsmentioning

confidence: 99%

Low temperature oxidation of linseed oil: a review

et al. 2012

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“…Extensive research has been conducted to establish structure-property relationships with epoxy-based polymers such as Avatrel Ò 2000P (Promerus LLC) and SU-8 (MicroChem). [1][2][3][4][5] Avatrel 2000P is a copolymer of alkyl norbornene and epoxide-functionalized norbornene monomers, as shown in Fig. 1.…”

Section: Introductionmentioning

confidence: 99%

Aqueous-Develop, Photosensitive Polynorbornene Dielectric: Properties and Characterization

Rajarathinam

Lightsey

Osborn

et al. 2009

Journal of Elec Materi

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The properties of a new aqueous-base-develop, negative-tone photosensitive polynorbornene have been characterized. High-aspect-ratio features of 7:1 (height:width) were produced in 70-lm-thick films in a single coat with straight side-wall profiles and high fidelity. The polymer films studied had contrast of 12.2 and low absorption coefficient. To evaluate the polymerÕs suitability to microelectronics applications, epoxy crosslinking reactions were studied as a function of processing condition through Fourier-transform infrared spectroscopy, nanoindentation, and dielectric measurements. The fully crosslinked films had an elastic modulus of 2.9 GPa and hardness of 0.18 GPa.

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“…It also confirms that the reaction of epoxide groups with NaCp was not completed. It is interesting that the evolution of the monomer GMA is not observed, as it is in the case of primary microspheres, so it can be concluded that depolymerization does not take place for the material modified with cyclopentadienyl group but the degradation proceeds according to the chain scission starting with the ether bond cleavage at glycidyl moiety [27]. At 412°C, the emission of acrolein is still observed; however, new absorption bands in the spectrum region of methylene and methyl groups vibrations (3015-2870 cm -1 ), and at 3099 cm -1 (characteristic of -CH=CH 2 vibration) appear.…”

Section: Resultsmentioning

confidence: 99%

Investigation of the thermal properties of glycidyl methacrylate–ethylene glycol dimethacrylate copolymeric microspheres modified by Diels–Alder reaction

Grochowicz

Pączkowski

Gawdzik

2017

J Therm Anal Calorim

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The study describes the thermal properties of functional microspheres composed of glycidyl methacrylate (GMA) and crosslinking agent ethylene glycol dimethacrylate (EGDMA). Copolymeric poly(GMA-co-EGDMA) microspheres were prepared via suspensionemulsion polymerization in the presence of toluene and decan-1-ol as porogens. In order to introduce functional groups, the porous methacrylate network was modified by epoxy ring opening with the use of sodium cyclopentadienide and then the Diels-Alder addition with maleic anhydride. The thermal properties of poly(GMA-co-EGDMA) materials were evaluated by thermogravimetry and differential scanning calorimetry. By TG/FTIR, it was observed that new functional materials exhibited multistaged decomposition patterns, different from parent poly(GMA-co-EGDMA) microspheres. The synthesized poly(GMA-co-EGDMA) microspheres exhibited rather high thermal stability in inert atmosphere. Their initial decomposition temperature determined at the temperature of 2% of mass loss was about 210°C; however, after the chemical modification it was slightly lower. The thermal degradation of parent poly(GMA-co-EGDMA) copolymer runs mainly according to the depolymerization mechanism, while functionalized by cyclopentadienyl group and maleic anhydride microspheres decompose through the chain scission mechanism.

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Crosslinking and decomposition reactions of epoxide functionalized polynorbornene. Part I. FTIR and thermogravimetric analysis

Cited by 50 publications

References 12 publications

Low temperature oxidation of linseed oil: a review

Low temperature oxidation of linseed oil: a review

Aqueous-Develop, Photosensitive Polynorbornene Dielectric: Properties and Characterization

Investigation of the thermal properties of glycidyl methacrylate–ethylene glycol dimethacrylate copolymeric microspheres modified by Diels–Alder reaction

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